# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p
_database_code_depnum_ccdc_archive 'CCDC 1449079'
_audit_update_record             
;
2016-01-22 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        4a
_chemical_name_common            4a
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H13 Cl N2 O2, C H2 Cl2'
_chemical_formula_sum            'C23 H15 Cl3 N2 O2'
_chemical_formula_weight         457.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           ?
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   7.7032(10)
_cell_length_b                   16.441(2)
_cell_length_c                   14.9629(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1895.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2674
_cell_measurement_theta_min      2.743
_cell_measurement_theta_max      20.108

_exptl_crystal_description       block
_exptl_crystal_colour            clolorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9190
_diffrn_reflns_av_R_equivalents  0.1332
_diffrn_reflns_av_sigmaI/netI    0.1707
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3058
_reflns_number_gt                2069
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7139(7) 0.6810(3) 1.0536(5) 0.0382(14) Uani 1 1 d . . .
C2 C 0.7757(9) 0.6909(3) 1.1354(5) 0.0469(15) Uani 1 1 d . . .
H2 H 0.8054 0.7427 1.1549 0.056 Uiso 1 1 calc R . .
C3 C 0.7967(9) 0.6260(4) 1.1916(5) 0.0592(19) Uani 1 1 d . . .
H3 H 0.8383 0.6338 1.2493 0.071 Uiso 1 1 calc R . .
C4 C 0.7571(10) 0.5522(4) 1.1630(5) 0.0594(19) Uani 1 1 d . . .
H4 H 0.7734 0.5080 1.2008 0.071 Uiso 1 1 calc R . .
C5 C 0.6924(7) 0.5396(3) 1.0786(5) 0.0494(18) Uani 1 1 d . . .
C6 C 0.6710(7) 0.6056(3) 1.0219(5) 0.0424(15) Uani 1 1 d . . .
C7 C 0.5645(10) 0.5265(3) 0.9132(5) 0.0619(19) Uani 1 1 d . . .
H7 H 0.5204 0.5204 0.8557 0.074 Uiso 1 1 calc R . .
C8 C 0.5823(10) 0.4583(3) 0.9651(7) 0.070(2) Uani 1 1 d . . .
H8 H 0.5504 0.4076 0.9430 0.084 Uiso 1 1 calc R . .
C9 C 0.6445(9) 0.4653(3) 1.0461(7) 0.063(2) Uani 1 1 d . . .
H9 H 0.6562 0.4194 1.0818 0.076 Uiso 1 1 calc R . .
C10 C 0.5212(6) 0.7874(2) 1.0157(4) 0.0325(12) Uani 1 1 d . . .
C11 C 0.3812(7) 0.7426(3) 1.0403(4) 0.0375(14) Uani 1 1 d . . .
H11 H 0.3928 0.6864 1.0439 0.045 Uiso 1 1 calc R . .
C12 C 0.2264(7) 0.7759(3) 1.0598(4) 0.0405(14) Uani 1 1 d . . .
H12 H 0.1329 0.7433 1.0761 0.049 Uiso 1 1 calc R . .
C13 C 0.2094(7) 0.8575(3) 1.0554(4) 0.0373(13) Uani 1 1 d . . .
C14 C 0.3449(6) 0.9036(3) 1.0299(4) 0.0355(13) Uani 1 1 d . . .
H14 H 0.3323 0.9597 1.0255 0.043 Uiso 1 1 calc R . .
C15 C 0.4986(6) 0.8689(2) 1.0107(4) 0.0318(12) Uani 1 1 d . . .
C16 C 0.7997(7) 0.7688(3) 0.9386(4) 0.0361(13) Uani 1 1 d . . .
C17 C 0.7744(7) 0.8385(3) 0.8821(4) 0.0352(13) Uani 1 1 d . . .
C18 C 0.6995(7) 0.9085(3) 0.9055(4) 0.0341(13) Uani 1 1 d . . .
C19 C 0.6901(8) 0.9729(3) 0.8521(5) 0.0471(16) Uani 1 1 d . . .
H19 H 0.6365 1.0205 0.8712 0.056 Uiso 1 1 calc R . .
C20 C 0.7587(10) 0.9680(4) 0.7707(5) 0.0590(18) Uani 1 1 d . . .
H20 H 0.7503 1.0119 0.7318 0.071 Uiso 1 1 calc R . .
C21 C 0.8400(9) 0.8999(4) 0.7447(5) 0.0589(18) Uani 1 1 d . . .
H21 H 0.8917 0.8973 0.6886 0.071 Uiso 1 1 calc R . .
C22 C 0.8466(8) 0.8357(3) 0.7995(5) 0.0496(16) Uani 1 1 d . . .
H22 H 0.9016 0.7883 0.7807 0.060 Uiso 1 1 calc R . .
C23 C 0.2829(11) 0.7146(4) 0.8312(5) 0.069(2) Uani 1 1 d . . .
H23A H 0.1992 0.7279 0.8774 0.083 Uiso 1 1 calc R . .
H23B H 0.3780 0.6854 0.8591 0.083 Uiso 1 1 calc R . .
Cl1 Cl 0.1868(3) 0.65307(10) 0.75436(16) 0.0908(8) Uani 1 1 d . . .
Cl2 Cl 0.3595(3) 0.80137(14) 0.78626(18) 0.1001(8) Uani 1 1 d . . .
Cl3 Cl 0.01704(18) 0.89929(8) 1.08345(14) 0.0565(5) Uani 1 1 d . . .
N1 N 0.6053(7) 0.5983(2) 0.9393(4) 0.0489(13) Uani 1 1 d . . .
N2 N 0.6810(5) 0.7506(2) 1.0017(3) 0.0334(10) Uani 1 1 d . . .
O1 O 0.9244(5) 0.7262(2) 0.9299(3) 0.0484(10) Uani 1 1 d . . .
O2 O 0.6363(5) 0.91812(17) 0.9909(3) 0.0375(9) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.323(9) . ?
C1 C6 1.368(8) . ?
C1 N2 1.406(7) . ?
C2 C3 1.368(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.322(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(9) . ?
C4 H4 0.9300 . ?
C5 C9 1.365(9) . ?
C5 C6 1.386(8) . ?
C6 N1 1.341(8) . ?
C7 N1 1.282(7) . ?
C7 C8 1.372(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.309(12) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.354(6) . ?
C10 C11 1.356(7) . ?
C10 N2 1.388(6) . ?
C11 C12 1.344(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.351(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.345(7) . ?
C13 Cl3 1.686(5) . ?
C14 C15 1.345(7) . ?
C14 H14 0.9300 . ?
C15 O2 1.367(6) . ?
C16 O1 1.196(6) . ?
C16 N2 1.348(7) . ?
C16 C17 1.437(7) . ?
C17 C18 1.335(7) . ?
C17 C22 1.356(9) . ?
C18 C19 1.329(8) . ?
C18 O2 1.375(7) . ?
C19 C20 1.329(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.340(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.338(9) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 Cl2 1.684(7) . ?
C23 Cl1 1.701(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.3(6) . . ?
C2 C1 N2 118.4(5) . . ?
C6 C1 N2 120.1(6) . . ?
C1 C2 C3 121.0(6) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.3(7) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.3(6) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C9 C5 C4 124.0(7) . . ?
C9 C5 C6 116.7(8) . . ?
C4 C5 C6 119.2(5) . . ?
N1 C6 C1 119.5(5) . . ?
N1 C6 C5 122.6(6) . . ?
C1 C6 C5 117.9(7) . . ?
N1 C7 C8 123.7(8) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 119.3(6) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C5 120.5(7) . . ?
C8 C9 H9 119.8 . . ?
C5 C9 H9 119.8 . . ?
C15 C10 C11 116.7(5) . . ?
C15 C10 N2 122.5(4) . . ?
C11 C10 N2 120.7(4) . . ?
C12 C11 C10 122.9(4) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 118.7(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 Cl3 121.6(4) . . ?
C12 C13 Cl3 118.5(4) . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 121.4(4) . . ?
C14 C15 O2 118.6(4) . . ?
C10 C15 O2 119.9(4) . . ?
O1 C16 N2 119.4(5) . . ?
O1 C16 C17 120.8(5) . . ?
N2 C16 C17 119.8(4) . . ?
C18 C17 C22 116.5(5) . . ?
C18 C17 C16 126.3(6) . . ?
C22 C17 C16 117.0(5) . . ?
C19 C18 C17 123.5(6) . . ?
C19 C18 O2 116.6(5) . . ?
C17 C18 O2 119.7(5) . . ?
C18 C19 C20 118.7(6) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C21 120.2(6) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.9(7) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C17 121.1(6) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
Cl2 C23 Cl1 112.7(5) . . ?
Cl2 C23 H23A 109.0 . . ?
Cl1 C23 H23A 109.0 . . ?
Cl2 C23 H23B 109.0 . . ?
Cl1 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C7 N1 C6 117.1(6) . . ?
C16 N2 C10 127.7(4) . . ?
C16 N2 C1 116.5(4) . . ?
C10 N2 C1 115.5(4) . . ?
C15 O2 C18 114.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.072
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p
_database_code_depnum_ccdc_archive 'CCDC 1449087'
_audit_update_record             
;
2016-01-22 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;
_audit_creation_date             2015-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            3k
_chemical_name_systematic        3k
_chemical_formula_moiety         'C21 H12 Cl N3 O2'
_chemical_formula_sum            'C21 H12 Cl N3 O2'
_chemical_formula_weight         373.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1470(16)
_cell_length_b                   7.9449(18)
_cell_length_c                   16.405(4)
_cell_angle_alpha                101.767(2)
_cell_angle_beta                 96.018(2)
_cell_angle_gamma                106.7307(18)
_cell_volume                     860.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3273
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.550
_cell_measurement_theta_min      2.576
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8620
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.573
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2419
_reflns_number_total             3034
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1550
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2446(4) 0.2033(3) 1.00234(15) 0.0585(6) Uani 1 1 d . . . . .
H1 H 0.2440 0.0902 1.0097 0.070 Uiso 1 1 calc R . . . .
C2 C 0.2893(4) 0.3454(3) 1.07502(15) 0.0582(6) Uani 1 1 d . . . . .
H2 H 0.3190 0.3266 1.1283 0.070 Uiso 1 1 calc R . . . .
C3 C 0.2885(3) 0.5100(3) 1.06605(13) 0.0521(6) Uani 1 1 d . . . . .
H3 H 0.3168 0.6062 1.1134 0.063 Uiso 1 1 calc R . . . .
C4 C 0.2446(3) 0.5362(3) 0.98479(12) 0.0403(5) Uani 1 1 d . . . . .
C5 C 0.2415(3) 0.7035(3) 0.97001(14) 0.0510(6) Uani 1 1 d . . . . .
H5 H 0.2684 0.8033 1.0156 0.061 Uiso 1 1 calc R . . . .
C6 C 0.1998(3) 0.7215(3) 0.89015(14) 0.0503(6) Uani 1 1 d . . . . .
H6 H 0.1990 0.8333 0.8814 0.060 Uiso 1 1 calc R . . . .
C7 C 0.1579(3) 0.5715(3) 0.82054(13) 0.0428(5) Uani 1 1 d . . . . .
H7 H 0.1273 0.5839 0.7660 0.051 Uiso 1 1 calc R . . . .
C8 C 0.1621(3) 0.4084(2) 0.83301(12) 0.0371(5) Uani 1 1 d . . . . .
C9 C 0.2039(3) 0.3845(2) 0.91521(12) 0.0362(5) Uani 1 1 d . . . . .
C10 C -0.3795(3) 0.0199(3) 0.77082(15) 0.0539(6) Uani 1 1 d . . . . .
H10 H -0.4882 0.0510 0.7873 0.065 Uiso 1 1 calc R . . . .
C11 C -0.4000(3) -0.1584(3) 0.74191(14) 0.0580(6) Uani 1 1 d . . . . .
H11 H -0.5210 -0.2470 0.7378 0.070 Uiso 1 1 calc R . . . .
C12 C -0.2381(4) -0.2061(3) 0.71870(13) 0.0514(6) Uani 1 1 d . . . . .
H12 H -0.2483 -0.3272 0.6985 0.062 Uiso 1 1 calc R . . . .
C13 C -0.0626(3) -0.0718(2) 0.72603(11) 0.0378(5) Uani 1 1 d . . . . .
C14 C -0.0515(3) 0.1087(2) 0.75374(12) 0.0365(4) Uani 1 1 d . . . . .
C15 C 0.2535(3) 0.2654(3) 0.70509(13) 0.0435(5) Uani 1 1 d . . . . .
C16 C 0.1593(3) -0.0705(3) 0.63396(12) 0.0385(5) Uani 1 1 d . . . . .
C17 C 0.2216(3) 0.1096(3) 0.63069(12) 0.0392(5) Uani 1 1 d . . . . .
C18 C 0.2761(3) 0.1473(3) 0.55588(13) 0.0457(5) Uani 1 1 d . . . . .
H18 H 0.3191 0.2673 0.5523 0.055 Uiso 1 1 calc R . . . .
C19 C 0.2684(3) 0.0132(3) 0.48742(13) 0.0475(5) Uani 1 1 d . . . . .
H19 H 0.3029 0.0410 0.4375 0.057 Uiso 1 1 calc R . . . .
C20 C 0.2086(3) -0.1646(3) 0.49364(13) 0.0479(5) Uani 1 1 d . . . . .
C21 C 0.1540(3) -0.2093(3) 0.56627(13) 0.0451(5) Uani 1 1 d . . . . .
H21 H 0.1147 -0.3294 0.5699 0.054 Uiso 1 1 calc R . . . .
Cl1 Cl 0.19872(10) -0.33558(9) 0.40693(4) 0.0741(3) Uani 1 1 d . . . . .
N1 N -0.2080(3) 0.1544(2) 0.77670(12) 0.0494(5) Uani 1 1 d . . . . .
N2 N 0.1256(2) 0.2541(2) 0.76203(10) 0.0384(4) Uani 1 1 d . . . . .
N3 N 0.2034(3) 0.2174(2) 0.92457(11) 0.0475(5) Uani 1 1 d . . . . .
O1 O 0.1035(2) -0.11834(18) 0.70701(8) 0.0451(4) Uani 1 1 d . . . . .
O2 O 0.3939(2) 0.4027(2) 0.71330(11) 0.0683(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.401(3) . ?
C1 N3 1.314(3) . ?
C2 C3 1.347(3) . ?
C3 C4 1.408(3) . ?
C4 C5 1.405(3) . ?
C4 C9 1.417(3) . ?
C5 C6 1.358(3) . ?
C6 C7 1.407(3) . ?
C7 C8 1.361(3) . ?
C8 C9 1.413(3) . ?
C8 N2 1.448(2) . ?
C9 N3 1.366(2) . ?
C10 C11 1.358(3) . ?
C10 N1 1.354(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.368(3) . ?
C13 C14 1.389(3) . ?
C13 O1 1.389(2) . ?
C14 N1 1.339(3) . ?
C14 N2 1.419(2) . ?
C15 C17 1.496(3) . ?
C15 N2 1.372(3) . ?
C15 O2 1.223(2) . ?
C16 C17 1.385(3) . ?
C16 C21 1.385(3) . ?
C16 O1 1.392(2) . ?
C17 C18 1.389(3) . ?
C18 C19 1.366(3) . ?
C19 C20 1.381(3) . ?
C20 C21 1.374(3) . ?
C20 Cl1 1.735(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 125.1(2) . . ?
C3 C2 C1 118.6(2) . . ?
C2 C3 C4 119.9(2) . . ?
C3 C4 C9 117.28(19) . . ?
C5 C4 C3 123.38(19) . . ?
C5 C4 C9 119.33(19) . . ?
C6 C5 C4 120.93(19) . . ?
C5 C6 C7 120.26(19) . . ?
C8 C7 C6 120.0(2) . . ?
C7 C8 C9 121.22(17) . . ?
C7 C8 N2 120.78(18) . . ?
C9 C8 N2 117.99(17) . . ?
C8 C9 C4 118.23(17) . . ?
N3 C9 C4 122.70(18) . . ?
N3 C9 C8 119.07(16) . . ?
N1 C10 C11 123.0(2) . . ?
C10 C11 C12 118.9(2) . . ?
C13 C12 C11 118.8(2) . . ?
C12 C13 C14 119.91(19) . . ?
C12 C13 O1 119.28(18) . . ?
O1 C13 C14 120.80(17) . . ?
C13 C14 N2 122.61(17) . . ?
N1 C14 C13 121.18(17) . . ?
N1 C14 N2 116.18(16) . . ?
N2 C15 C17 120.24(17) . . ?
O2 C15 C17 118.63(18) . . ?
O2 C15 N2 121.12(19) . . ?
C17 C16 O1 120.71(16) . . ?
C21 C16 C17 121.92(18) . . ?
C21 C16 O1 117.36(17) . . ?
C16 C17 C15 123.93(17) . . ?
C16 C17 C18 117.54(18) . . ?
C18 C17 C15 118.21(18) . . ?
C19 C18 C17 121.90(19) . . ?
C18 C19 C20 118.82(19) . . ?
C19 C20 Cl1 119.04(17) . . ?
C21 C20 C19 121.65(19) . . ?
C21 C20 Cl1 119.30(17) . . ?
C20 C21 C16 118.15(19) . . ?
C14 N1 C10 118.22(19) . . ?
C14 N2 C8 116.14(15) . . ?
C15 N2 C8 118.31(15) . . ?
C15 N2 C14 125.32(16) . . ?
C1 N3 C9 116.49(18) . . ?
C13 O1 C16 111.71(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
